A Working Sissy Girl

"I feel shameful, feel ashamed of myself, Mistress, for what I do, what I am." I drop the riding crop at his side. I reach down and run two of my fingers in the cum in his hand, bend forward and pull his chin up toward me. I smile down at him. I run my fingers around his slightly quivering lips, let them just tease inside his mouth...he wants to cry, I can tell. "You want to cry for mama, right, baby? It's okay. Come on, you're such a good little boy. Cry for mama." He starts to whimper and then cry softly. "Let it out, this makes your Mistress happy." I pat his head, watch him sob softly, real tears come down his fat cheeks.

"You know what your Mistress wants now, baby. You know." I watch as he licks the cum from his hand, tears in his eyes. He can't look at me. He truly is ashamed of himself. I say nothing, just watch as he cleans his hand with his eyes closed. When he finishes he keeps his head bowed.

I walk to the mini bar, pour a drink, bourbon. I check my make up in the mirror. Not a smudge, still the perfectly cute sissy girl I was when I walked in the hotel room a little over an hour ago. I look at him in the mirror. "You may dress, baby. I'm through with you for now." I look back at myself in the mirror. Black leather mini dress comes up around my neck at the top, shiny silver large hoop earrings, tight black spiky hair, curls up just around my ears, very nice. I look like a real girl. Just a hint of the sissy boy I actually am. I like that, really like that. I reach back and smooth the rear of my dress, check myself out in the mirror.

"You want a drink, honey?" I smile at him. I don't wait, I fix him a vodka, one ice cube, know what he likes. I walk to him as he is buttoning his shirt. Hand it to him. "You were wonderful today, really were. Did you have a good time?"

He takes the drink, "You know I do, just go through the adjustment period after all this over." He raised the glass to his lips, tosses the whole drink back and swallows.